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Tetra substituted chalcone derivative and preparing method and use

A chalcone derivative and disubstituted technology, which is applied in the field of organic compound synthesis, can solve problems such as the mechanism of action is not further elucidated, and achieve the effects of low production cost, mild reaction conditions and high yield

Inactive Publication Date: 2006-03-22
ZHEJIANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Boron-containing compounds have previously been used as fluorescent probes for the detection of fluorine compounds and sugars, but this paper only reported their anti-breast cancer activity without further elucidating their mechanism of action

Method used

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  • Tetra substituted chalcone derivative and preparing method and use
  • Tetra substituted chalcone derivative and preparing method and use
  • Tetra substituted chalcone derivative and preparing method and use

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] Example 1. 2-Hydroxy-4,6-dimethoxy-acetophenone (III): prepared by referring to the literature method (K.Y.T.Juntend et al, EP 0292576).

[0021] M.p.77-78℃

[0022] 1 HNMR (δ, CDCl 3 ): 14.06(s, 1H), 6.05(d, 1H, J=2.4Hz), 5.92(d, 1H, J=2.4Hz). 3.90(s, 3H), 3.62(s, 3H), 2.63(s , 3H)

Embodiment 2

[0023] Example 2, 2'-Hydroxy-4', 6'-dimethoxy-2-chloro-chalcone (IV): Refer to the literature method (Xiaoyong Bu et al, Synthesis, 1997, 11, 1246-1248) be made of.

[0024] M.p.123-124℃

[0025] 1 HNMR (δ, CDCl 3 ): 14.20(s, 1H), 8.12-8.16(d, 1H, J=15.6Hz), 7.85-7.89(d, 1H, J=15.2Hz), 7.68-7.70(m, 1H), 7.42-7.44( m, 1H), 7.26-7.31(m, 2H), 6.10-6.11(d, 1H, J=2.4Hz), 5.95-5.96(d, 1H, J=2.4Hz), 3.90(s, 3H), 3.84 (s, 3H).

Embodiment 3

[0026] Example 3, 2'-hydroxyl-3'-(4-methylpiperazin-1-yl-methyl)-4',6'-dimethoxy-2-chloro-chalcone (Va):

[0027] Compound IV 1.59g (4.99mmol), formaldehyde aqueous solution 1.24g (15.30mmol), N-methylpiperazine 1.10g (10.98mmol), methanol 12.5ml and hydrochloric acid were added dropwise into the reaction flask, and refluxed for 2h. Cool, recover the solvent under reduced pressure, dilute with water, basify, extract with dichloromethane, wash with saturated sodium chloride, dry over anhydrous sodium sulfate, recover the solvent under reduced pressure, column chromatography (eluent: petroleum ether: ethyl acetate: Triethylamine=200ml:400ml:9.6ml) to obtain 1.17g of yellow solid, yield 56%. m.p.146-148°C.

[0028] 1 HNMR (δ, CDCl 3 ): 7.96-8.00(d, 1H, J=15.6Hz), 7.67-7.70(m, 1H), 7.38-7.42(d, 1H, J=15.6Hz), 7.39-7.41(m, 1H), 7.26- 7.29(m, 2H), 6.00(s, 1H), 3.86(s, 3H), 3.85(s, 3H), 3.71(s, 2H), 2.60-2.61(m, 4H), 2.44-2.45(m, 4H), 2.26(s, 3H).

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Abstract

The present invention provides 2-hydroxy-3-amino methylene-4, 6-dibubstituted chalcone derivative with the structural general expression as shown. The preparation process includes the following steps: Lewis acid catalyzed reaction of compound I and anhydrous methy1cyanide inside inert solvent to obtain intermediate trihydroxy acetophenone amide hydrochloride; further acid hydrolysis to obtain compound II; selective etherification with alkylation reagent under alkaline cddn to obtain compound III; condensation with aromatic aldehyde under alkaline condition to obtain compound IV; and reaction with secondary amine in the presence of acid and formaldehyde to produce destination compound V. The present invention provides completely new structure compounds with powerful tumor cell inhibiting effect and IC50 value up to 0.8 micron, and capable of being used in preparing antitumor medicine.

Description

technical field [0001] The present invention belongs to the synthesis of organic compounds, and relates to the preparation method of four-substituted chalcone derivatives, in particular to the preparation method of 2-hydroxy-3-amine methylene-4,6-disubstituted chalcone derivatives, and in Application in the preparation of antitumor drugs. Background technique [0002] Chalcone derivatives have antitumor effects. In 2001, C. Pouget et al. reported that a series of disubstituted or trisubstituted 2-hydroxychalcone derivatives have antitumor effects, among which 2', 4'-dihydroxychalcone and 2'-hydroxyl-4' - Methoxychalcone is effective against breast cancer cell MCF-7, its IC 50 The values ​​are 16.3 and 18.3 μM, respectively. The structure of the chalcone derivatives provided in this paper is relatively common, and the aromatic ring is unsubstituted or only substituted with oxygen-containing functional groups (hydroxyl and methoxy groups). At the same time, the author has o...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C225/16C07C229/22C07D295/112A61K31/135A61K31/195A61K31/495A61K31/445A61K31/40A61K31/53A61P35/00
Inventor 刘滔胡永洲何俏军杨波
Owner ZHEJIANG UNIV